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Alkanes Alkenes Alkynes
Alkanes Alkenes Alkynes
Alkanes Alkenes Alkynes
3 The alkane CH3CH2C(CH3)2CH2CH(CH3)2 has how many 1º, 2º. 3º & 4º carbon atoms?
1º 2º 3º 4º
A) 4 2 2 1
B) 5 1 2 1
C) 5 2 1 1
D) 6 1 1 1
5 Which isomer of hexane has only two different sets of structurally equivalent hydrogen atoms.?
A) 2,2-dimethylbutane
B) 2-methylpentane
C) 3-methylpentane
D) 2,3-dimethylbutane
6 Limiting your answer to cycloalkanes and ignoring stereoisomers, how many C6H12 constitutional isomers are there?
A) 6
B) 9
C) 12
D) 13
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C) 2,3-dimethyl-5-hexene
D) 4-methyl-4-isopropyl-1-butene
10 Which of the following represents the most stable conformation of all cis-1,2,4-trimethylcyclohexane?
11 A C6H12 compound reacts with ozone to yield a single C3H6O product. Gas phase free radical bromination of the
hydrocarbon gives a single C6H11Br product. A likely identification of this compound is ..
A) cyclohexane
B) cyclohexene
C) 3-hexene
D) 2,3-dimethyl-2-butene
12 The terpene ocimene has the IUPAC name (3E)-3,7-dimethyl-1,3,6-octatriene, what is the structural formula of this
compound?
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16 Which of the following C6H12 isomers has the largest heat of combustion?
A) cyclohexane
B) methylcyclopentane
C) ethylcyclobutane
D) propylcyclopropane
17 The radical halogenation of 2-methylpropane gives two products: (CH3)2CHCH2X (minor) and (CH3)3CX (major)
Chlorination gives a larger amount of the minor product than does bromination, Why?
A) Bromine is more reactive than chlorine and is able to attack the less reactive 3º C-H.
B) Bromine atoms are less reactive (more selective) than chlorine, and preferentially attack the weaker 3º C-H
bond.
C) The methyl groups are more hindered to attack by the larger bromine atom.
D) Bromination is reversible and the more stable 3º-alkyl bromide is formed exclusively.
18 A tertiary carbocation (carbonium ion) is more stable than either a secondary or primary carbocation because ...
A) it carries three positive charges
B) it has a pyramidal configuration
C) it has a trigonal planar configuration
D) it possesses three electron-donating substituent groups
20 Which of the following olefins would you expect to react most rapidly with concentrated sulphuric acid ?
A) H2C=CH2
B) (CH3)2C=CH2
C) Cl2C=CCl2
D) CF3CH=CH2
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26 Treatment of 1-methylcyclohexene with an ether solution of diborane ( B2H6 ), followed by reaction with alkaline
H2O2 produces what product?
A) 1-methylcyclohexanol
B) cis-1-methylcyclohexane-1,2-diol
C) cis-2-methylcyclohexanol
D) trans-2-methylcyclohexanol
27 Which of the following will be the kinetically favored product from the depicted reaction ?
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28 Two C4H6 isomers give the same C4H8O product from HgSO4 catalyzed hydration in aqueous acid.
However, these isomers give different C4H6Br4 products with excess bromine.
What are these isomeric hydrocarbons?
A) cyclobutene and methylenecyclopropane
B) 1,2-butadiene and 1,3-butadiene
C) 1-butyne and 2-butyne
D) 2-butyne and cyclobutene
30 Two C5H8 isomers undergo catalytic (Pt) hydrogenation to form the same C5H10 product. On ozonolysis followed
by oxidative workup (H2O2), one isomer gave a C5H8O4 diacid, while the other isomer gave a C5H8O3 ketoacid.
Which of the following isomeric pairs correspond to this evidence?
A) cyclopentene and 1-pentyne
B) cyclopentene and 1-methylcyclobutene
C) 1-methylcyclobutene and 3-methylcyclobutene
D) cyclopentene and 3-methylcyclobutene
31 Considering that the angles of a regular pentagon are 108º, why is cyclopentane not planar?
A) all the carbons are sp2 hybridized, so there is considerable angle strain.
B) The C-C bonds are formed by overlap of p-orbitals, so the 90º angle results in large angle strain.
C) The cyclic overlap of bonding orbitals results in anti-aromaticity destabilization.
D) The five C-C bonds have eclipsing strain.
33 Reaction of 1-hexene with NBS (N-bromosuccinimide) forms two isomeric bromohexenes, one of which is 3-
bromo-1-hexene.
Which of the following is the other isomer?
A) 1-bromo-2-hexene.
B) 6-bromo-1-hexene.
C) 1-bromo-1-hexene.
D) 2-bromo-1-hexene.
34 A C6H10 hydrocarbon forms an insoluble silver salt when treated with silver nitrate in ethanolic ammonia.
Acid catalyzed hydration with a HgSO4 catalyst generates a single C6H12O ketone, and pemanganate oxidation yields
a C5H10O2 carboxylic acid
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35 Peroxide induced reaction of carbon tetrachloride with 1-butene produces which of the following?
A) 1,1,1,3-tetrachloropentane.
B) 1,1,1,2-tetrachloropentane.
C) 1-chloro-2-trichloromethylbutane.
D) 1,1-dichloro-2-ethylcyclopropane.
36 Which of the following isomeric hexenes will have the smallest heat of hydrogenation?
A) 4-methyl-1-pentene.
B) (E)-4-methyl-2-pentene.
C) (Z)-4-methyl-2-pentene.
D) 2-methyl-2-pentene.
37 A C8H14 hydrocarbon (X) is reduced by sodium in liquid ammonia to a single C8H16 product (Y).
Both of these compounds undergo hydrogenation (Pt catalyst) to give 2,5-dimethylhexane.
Ozonolysis of Y with an oxidative workup produces a single C4H8O2 carboxylic acid.
Reaction of Y with perbenzoic acid (C6H5CO3H) gives a chiral C8H14O product, but reaction with bromine gives an
achiral C8H14Br2 product
What are X and Y?
A) X is 2,5-dimethyl-3-hexyne ; Y is cis-2,5-dimethyl-3-hexene.
B) X is 2,5-dimethyl-3-hexyne ; Y is trans-2,5-dimethyl-3-hexene.
C) X is 2.5-dimethyl-1,5-hexadiene ; Y is 2,5-dimethyl-3-hexyne.
D) X is 2,5-dimethyl-2,4-hexadiene ; Y is cis-2,5-dimethyl-3-hexene.
38 Which of the following compounds has two or more conjugated double bonds?
39 What reagent(s) would best achieve conversion of 3,3-dimethyl-1-butyne to the aldehyde (CH3)3CCH2CHO?
A) H3O(+) and catalytic Hg(+2)
B) (i) R2BH in ether ( R=C5H11 )
(ii) H2O2 and aqueous NaOH
C) KMnO4 in aqueous NaOH
D) (i) HOBr
(ii) aqueous NaOH
40 Which of the following dienes would best serve as a diene in a Diels-Alder reaction?
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41 Which of the following is the most likely product of this Diels-Alder reaction?
42 Which of the following is the most likely product of this Diels-Alder reaction?
43 Reaction of 1,1-dibromopentane with three equivalents of NaNH2 in ether is followed by treatment with 0.1M HCl
at 0º C.
What is the product?
A) cyclopentene.
B) 1,2-pentadiene.
C) 2-pentyne.
D) 1-pentyne.
44 Which of the following reagents and conditions would best serve to convert 1-butyne to 1,1-dibromobutane?
A) 2 equivalents of HBr, no peroxides.
B) 2 equivalents of HBr, with peroxides.
C) 1 equivalent of Br2.
D) 2 equivalents of Br2 followed by i equivalent of KOH.
45 What is the relative rate of addition of HBr to I: 1,3-pentadiene; II: 1,4-pentadiene; and III: 1-pentyne?
A) I > II > III.
B) III > II > I.
C) II > I > III.
D) III > I > II.
46 A chiral C6H12 hydrocarbon undergoes catalytic hydrogenation to yield an achiral C6H14 product. What is the
starting compound?
A) cis-2-hexene
B) 3-methyl-2-pentene
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C) 4-methyl-2-pentene
D) 3-methyl-1-pentene
47 Reaction of 3,3,6,6-tetramethyl-1,4-cyclohexadiene, first with excess aqueous mercuric acetate, then followed by
sodium borohydride reduction, produces a mixture of isomeric C10H20O2 alcohols.
Excluding enantiomers, how many isomeric products may be formed in this reaction?
A) 2
B) 4
C) 6
D) 8
51 What structural change takes place when an alkene undergoes a Simmons-Smith reaction?
A) addition of ethene gives a cyclobutane derivative.
B) the double bond is shifted to a more substituted location.
C) the double bond is converted to a triple bond.
D) a methylene group is added to give a cyclopropane derivative.
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53 Which one of the following compounds contains the greatest number of sp2 hybridized carbon atoms?
A) 1,4-Cycloheptadiene
B) 2,5-dimethyl-2,3,4-hexatriene
C) Phenylacetylene
D) 1,1-diallyl-3,3-divinylcyclobutane
54 Which one of the following compounds contains the greatest number of sp hybridized carbon atoms?
A) 1,4-Cyclooctadiene
B) 2,5-dimethyl-2,3,4-hexatriene
C) Phenylacetylene
D) 1,1-diallyl-3,3-divinylcyclobutane
55 Which one of the following compounds contains the greatest number of sp3 hybridized carbon atoms?
A) 1,4-Cyclooctadiene
B) 2,5-dimethyl-2,3,4-hexatriene
C) Phenylacetylene
D) 1,1-diallyl-3,3-divinylcyclobutane
57 Compound Z, C8H14, reacts with excess hydrogen and a Pt catalyst to give 2,5-dimethylhexane as the only
product.
Z diplays three 13C nmr signals, all at higher field than 100 ppm, and does not absorb in the UV at wavelengths
greater than 200 nm.
Oxidation of Z by either ozone or potassium permanganate produces a single C4H8O2 carboxylic acid. Deduce the
structure of Z.
A) 2,5-dimethyl-3-hexyne
B) trans-2,5-dimethyl-3-hexene
C) cis-2,5-dimethyl-3-hexene
D) 2,5-dimethyl-2,4-hexadiene
58 Which of the following is the correct configurational prefix for the following diene?
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